KR101895148B1 - 유기 전계 발광 소자용의 유기 이리듐 착체 - Google Patents
유기 전계 발광 소자용의 유기 이리듐 착체 Download PDFInfo
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- KR101895148B1 KR101895148B1 KR1020167035618A KR20167035618A KR101895148B1 KR 101895148 B1 KR101895148 B1 KR 101895148B1 KR 1020167035618 A KR1020167035618 A KR 1020167035618A KR 20167035618 A KR20167035618 A KR 20167035618A KR 101895148 B1 KR101895148 B1 KR 101895148B1
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- South Korea
- Prior art keywords
- organic
- mmol
- iridium complex
- ligand
- diketone
- Prior art date
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- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 91
- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 88
- 239000003446 ligand Substances 0.000 claims abstract description 59
- 238000005401 electroluminescence Methods 0.000 claims abstract description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000006862 quantum yield reaction Methods 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 239000010409 thin film Substances 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 26
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 76
- 239000002904 solvent Substances 0.000 description 51
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- 239000002243 precursor Substances 0.000 description 45
- 239000000203 mixture Substances 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 32
- 238000003786 synthesis reaction Methods 0.000 description 31
- 150000001875 compounds Chemical class 0.000 description 27
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 24
- 229910052938 sodium sulfate Inorganic materials 0.000 description 24
- 235000011152 sodium sulphate Nutrition 0.000 description 24
- 238000001816 cooling Methods 0.000 description 23
- 238000001914 filtration Methods 0.000 description 23
- 238000005481 NMR spectroscopy Methods 0.000 description 22
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 22
- 239000010410 layer Substances 0.000 description 21
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 20
- 239000012299 nitrogen atmosphere Substances 0.000 description 20
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 16
- 229940093475 2-ethoxyethanol Drugs 0.000 description 16
- 239000000706 filtrate Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000004440 column chromatography Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 12
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 229910000029 sodium carbonate Inorganic materials 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- 239000011259 mixed solution Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- -1 butoxy-substituted benzene rings Chemical group 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- 150000002503 iridium Chemical class 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 125000002524 organometallic group Chemical group 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 230000003993 interaction Effects 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 5
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 4
- 230000005284 excitation Effects 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- LNJXVUXPFZKMNF-UHFFFAOYSA-K iridium(3+);trichloride;trihydrate Chemical compound O.O.O.Cl[Ir](Cl)Cl LNJXVUXPFZKMNF-UHFFFAOYSA-K 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- BRZLLJSRIPVXFR-UHFFFAOYSA-N 1-dibenzofuran-4-ylisoquinoline Chemical compound C1=CC=C2C(C3=C4OC=5C(C4=CC=C3)=CC=CC=5)=NC=CC2=C1 BRZLLJSRIPVXFR-UHFFFAOYSA-N 0.000 description 3
- UCVINTIEPYMTAQ-UHFFFAOYSA-N 2-dibenzofuran-4-ylquinoline Chemical compound C1=CC=CC2=NC(C3=C4OC=5C(C4=CC=C3)=CC=CC=5)=CC=C21 UCVINTIEPYMTAQ-UHFFFAOYSA-N 0.000 description 3
- 0 CCc(cc1)c(C)c2c1-c1ccccc1*2 Chemical compound CCc(cc1)c(C)c2c1-c1ccccc1*2 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 238000005979 thermal decomposition reaction Methods 0.000 description 3
- CCQKWSZYTOCEIB-UHFFFAOYSA-N 1,1,4,4-tetramethyl-2,3-dihydronaphthalene Chemical compound C1=CC=C2C(C)(C)CCC(C)(C)C2=C1 CCQKWSZYTOCEIB-UHFFFAOYSA-N 0.000 description 2
- AVTSEHYNSNELMQ-UHFFFAOYSA-N 1,3-bis(3,5-ditert-butylphenyl)propane-1,3-dione Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(C(=O)CC(=O)C=2C=C(C=C(C=2)C(C)(C)C)C(C)(C)C)=C1 AVTSEHYNSNELMQ-UHFFFAOYSA-N 0.000 description 2
- MSQCQINLJMEVNJ-UHFFFAOYSA-N 1-chloroisoquinoline Chemical compound C1=CC=C2C(Cl)=NC=CC2=C1 MSQCQINLJMEVNJ-UHFFFAOYSA-N 0.000 description 2
- FYYZLNTYBLXDKM-UHFFFAOYSA-N 1-dibenzothiophen-4-ylisoquinoline Chemical compound C1=CC=C(C=2SC3=C(C=21)C=CC=C3)C1=NC=CC2=CC=CC=C12 FYYZLNTYBLXDKM-UHFFFAOYSA-N 0.000 description 2
- OFUFXTHGZWIDDB-UHFFFAOYSA-N 2-chloroquinoline Chemical compound C1=CC=CC2=NC(Cl)=CC=C21 OFUFXTHGZWIDDB-UHFFFAOYSA-N 0.000 description 2
- FYLUMWHKJHEKGF-UHFFFAOYSA-N 2-dibenzothiophen-4-ylquinoline Chemical compound C1=CC=CC2=NC(C3=C4SC=5C(C4=CC=C3)=CC=CC=5)=CC=C21 FYLUMWHKJHEKGF-UHFFFAOYSA-N 0.000 description 2
- NCTSLPBQVXUAHR-UHFFFAOYSA-N 3,5-ditert-butylbenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(C)(C)C)=C1 NCTSLPBQVXUAHR-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 2
- ZEIOQJMJXFVPOG-UHFFFAOYSA-N methyl 3,5-ditert-butylbenzoate Chemical compound COC(=O)C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1 ZEIOQJMJXFVPOG-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000000103 photoluminescence spectrum Methods 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 239000013585 weight reducing agent Substances 0.000 description 2
- WZSMQEXDKGEYOW-UHFFFAOYSA-N 1-(3,5-ditert-butylphenyl)ethanone Chemical compound CC(=O)C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1 WZSMQEXDKGEYOW-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SURCGQGDUADKBL-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-5-nitrobenzo[de]isoquinoline-1,3-dione Chemical compound [O-][N+](=O)C1=CC(C(N(NCCO)C2=O)=O)=C3C2=CC=CC3=C1 SURCGQGDUADKBL-UHFFFAOYSA-N 0.000 description 1
- AWKVVRUTLJCPPO-UHFFFAOYSA-N 3-oxo-2,3-diphenylpropanal Chemical compound C=1C=CC=CC=1C(C=O)C(=O)C1=CC=CC=C1 AWKVVRUTLJCPPO-UHFFFAOYSA-N 0.000 description 1
- TVPKSUOSVXEGPT-UHFFFAOYSA-N CC(C)=O.C(CCC)C=1C(=C(C(=O)O)C=CC1)CCCC Chemical compound CC(C)=O.C(CCC)C=1C(=C(C(=O)O)C=CC1)CCCC TVPKSUOSVXEGPT-UHFFFAOYSA-N 0.000 description 1
- BFALZKKYACXBLW-UHFFFAOYSA-N CCCCCc1c(C(C)(C)C)ccc(C(CC(c2ccc(C(C)(C)C)cc2)=O)=O)c1 Chemical compound CCCCCc1c(C(C)(C)C)ccc(C(CC(c2ccc(C(C)(C)C)cc2)=O)=O)c1 BFALZKKYACXBLW-UHFFFAOYSA-N 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- AFVLVVWMAFSXCK-VMPITWQZSA-N alpha-cyano-4-hydroxycinnamic acid Chemical compound OC(=O)C(\C#N)=C\C1=CC=C(O)C=C1 AFVLVVWMAFSXCK-VMPITWQZSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000003097 hole (electron) Substances 0.000 description 1
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- 238000001748 luminescence spectrum Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000001254 matrix assisted laser desorption--ionisation time-of-flight mass spectrum Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 description 1
- CCWOAEHVQLCSTC-UHFFFAOYSA-N methyl 2,3-dibutylbenzoate Chemical compound C(CCC)C=1C(=C(C(=O)OC)C=CC=1)CCCC CCWOAEHVQLCSTC-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
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- 150000002894 organic compounds Chemical class 0.000 description 1
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- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
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- 239000002356 single layer Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
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- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- IDSWJMDPKPOHRX-UHFFFAOYSA-N thiophen-3-yloxyboronic acid Chemical compound OB(O)OC=1C=CSC=1 IDSWJMDPKPOHRX-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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Applications Claiming Priority (5)
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| JPJP-P-2014-121997 | 2014-06-13 | ||
| JP2014121997 | 2014-06-13 | ||
| JP2015045467A JP5897171B2 (ja) | 2014-06-13 | 2015-03-09 | 有機電界発光素子用の有機イリジウム錯体 |
| JPJP-P-2015-045467 | 2015-03-09 | ||
| PCT/JP2015/066570 WO2015190464A1 (ja) | 2014-06-13 | 2015-06-09 | 有機電界発光素子用の有機イリジウム錯体 |
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| KR20170012344A KR20170012344A (ko) | 2017-02-02 |
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| KR (1) | KR101895148B1 (ja) |
| CN (1) | CN106459114B (ja) |
| DE (1) | DE112015002807T5 (ja) |
| TW (1) | TWI621621B (ja) |
| WO (1) | WO2015190464A1 (ja) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2016031840A1 (ja) * | 2014-08-28 | 2016-03-03 | 田中貴金属工業株式会社 | 有機電界発光素子用の有機イリジウム錯体 |
| US11744143B2 (en) | 2016-08-25 | 2023-08-29 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound |
| KR102395780B1 (ko) | 2017-03-23 | 2022-05-09 | 삼성전자주식회사 | 유기금속 화합물, 이를 포함한 유기 발광 소자 |
| CN111377969B (zh) * | 2018-12-27 | 2020-12-04 | 广东阿格蕾雅光电材料有限公司 | 一种有机金属化合物及其应用 |
| US11239435B2 (en) * | 2019-01-21 | 2022-02-01 | Luminescence Technology Corp. | Iridium complex and organic electroluminescence device using the same |
| JP7195952B2 (ja) | 2019-01-30 | 2022-12-26 | 田中貴金属工業株式会社 | 有機電界発光素子用の有機イリジウム錯体 |
| CN112830943B (zh) | 2019-11-25 | 2022-12-23 | 广东阿格蕾雅光电材料有限公司 | 一种化合物及其应用 |
| CN113683643A (zh) * | 2020-05-19 | 2021-11-23 | 北京夏禾科技有限公司 | 一种有机发光材料 |
| DE102021112841A1 (de) * | 2020-05-19 | 2021-11-25 | Beijing Summer Sprout Technology Co., Ltd. | Organisches, Licht emittierendes Material |
| CN111620910B (zh) * | 2020-06-03 | 2023-09-05 | 广东阿格蕾雅光电材料有限公司 | 一种金属络合物及其应用 |
| CN113831369A (zh) * | 2020-06-23 | 2021-12-24 | 广东阿格蕾雅光电材料有限公司 | 一种金属铱络合物及其应用 |
| CN114478637B (zh) * | 2020-10-23 | 2023-09-05 | 北京绿人科技有限责任公司 | 一种含1,3-二酮配体的化合物及其应用、一种有机致电发光器件 |
| US20240130216A1 (en) | 2020-12-04 | 2024-04-18 | Guangdong Aglaia Optoelectronic Materials Co., Ltd | Iridium complex and application thereof |
| CN114591371A (zh) | 2020-12-04 | 2022-06-07 | 广东阿格蕾雅光电材料有限公司 | 一种金属络合物及其应用 |
| CN117126204A (zh) * | 2021-11-09 | 2023-11-28 | 广东阿格蕾雅光电材料有限公司 | 一种金属铱络合物及其应用 |
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| JP2012077069A (ja) * | 2010-09-09 | 2012-04-19 | Osaka Prefecture Univ | ビス（アミノビフェニルエチニル）系化合物、青色蛍光色素および有機ｅｌ素子 |
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| JP4307000B2 (ja) * | 2001-03-08 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物、電界発光素子及び表示装置 |
| TW200514836A (en) * | 2003-06-18 | 2005-05-01 | Hitachi Chemical Co Ltd | Copolymer containing metal coordination compound and organic electroluminescence device using the same |
| JP4484464B2 (ja) | 2003-07-16 | 2010-06-16 | 三洋電機株式会社 | 発光材料及び発光素子 |
| JP2008222635A (ja) | 2007-03-13 | 2008-09-25 | Osaka Prefecture Univ | 金属錯体化合物、色素および有機電界発光素子 |
| US8722205B2 (en) * | 2009-03-23 | 2014-05-13 | Universal Display Corporation | Heteroleptic iridium complex |
| KR102191108B1 (ko) | 2013-10-18 | 2020-12-15 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 소자 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2012077069A (ja) * | 2010-09-09 | 2012-04-19 | Osaka Prefecture Univ | ビス（アミノビフェニルエチニル）系化合物、青色蛍光色素および有機ｅｌ素子 |
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| Title |
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| Journal of Photopolymer Science and Technology, Vol.21, pp.323-325 (2008)* |
Also Published As
| Publication number | Publication date |
|---|---|
| TWI621621B (zh) | 2018-04-21 |
| DE112015002807T5 (de) | 2017-03-02 |
| CN106459114B (zh) | 2019-08-27 |
| KR20170012344A (ko) | 2017-02-02 |
| US20170200907A1 (en) | 2017-07-13 |
| JP2016015468A (ja) | 2016-01-28 |
| CN106459114A (zh) | 2017-02-22 |
| TW201602119A (zh) | 2016-01-16 |
| JP5897171B2 (ja) | 2016-03-30 |
| US9793499B2 (en) | 2017-10-17 |
| WO2015190464A1 (ja) | 2015-12-17 |
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